Tetrakis (hydroxyphenyl)alkane can be used as a host compound in polymolecular clathrate compounds. For example, 1,1,2,2-tetrakis (4-hydroxyphenyl)ethane selectively forms clathrate compounds (compounds having an inclusion of guest molecule in a cavity formed by the host molecule) with various organic guest compounds and therefore it's application is expected in technical fields such as selective separation, chemical stabilization, prevention of vaporization and pulverization.
Up until the present, as a method for producing tetrakis(hydroxyphenyl)alkanes, a method of condensing phenol and glyoxal in acetic acid in a temperature range of 2 to 10° C. in the presence of sulfuric acid is known (for example, Non-Patent Document 1).
In addition, there is a method for producing tetrakis(hydroxyphenyl)alkanes by condensing glyoxal and phenol in excess with respect to glyoxal in a temperature range of 100 to 180° C. in the presence of hydrochloric acid (for example, Patent Document 1) or a method characterized by condensing phenol and a dialdehyde or derivatives thereof in the presence of sulfuric acid and phosphoric acid (for example, Patent Document 2).
However as shown by the method disclosed in Patent Document 1, a reaction using a single sulfuric acid catalyst is difficult to control and tends to be associated with side reactions or runaway reactions. Furthermore although reactions at high temperatures using phenol in excess have characters such as no requirement of reaction solvents, a short reaction time and a low cost, there is a tendency for side reactions and high yields are not expected. Moreover there is the problem that it is extremely difficult to eliminate multiple products resulting from such side reactions.
As shown by the method disclosed in Patent Document 2, side reactions can be suppressed by condensation in the presence of a mixed acidic catalyst comprising sulfuric acid and phosphoric acid resulting in highly efficient and selective production of tetrakis(hydroxyphenyl)alkanes. However, the yield is on the order of 40 to 70% and the reaction time requires from several to tens of hours.
As shown by the method disclosed in Patent Document 3, a compound having a tetrakis phenyl backbone combining ester groups with phenyl groups can be produced by a coupling reaction using a zinc catalyst. However this method requires a 24-hour reflux process, and has a long reaction time and a low yield.    Non-Patent Document 1:
Monatshefte fur Chem I e., 82, 652 (1951)    Patent Document 1:
Japanese Unexamined Patent Application, First Publication No. Sho-57-65716    Patent Document 2:
Japanese Unexamined Patent Application, First Publication No. Hei-7-076538    Patent Document 3:
WO 00/20372